N,N-Dimethylaniline → HCID 10269744, compound

HRID 2180914Notes

Reaction equation

HRID 2180914 reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][C:5]2[S:6][C:7]3[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=3[C:9](=O)[NH:10][C:4]=2[CH:3]=1.P(Cl)(Cl)(Cl)=O.CN(C)C1C=CC=CC=1.[CH2:32]([N:34]1[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]1)[CH3:33]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:17]=[CH:16][C:5]2[S:6][C:7]3[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=3[C:9]([N:37]3[CH2:38][CH2:39][N:34]([CH2:32][CH3:33])[CH2:35][CH2:36]3)=[N:10][C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 949N,N-DimethylanilineHCID 24813Phosphorus oxychlorideHCID 791961-EthylpiperazineHCID 8271058-chlorodibenzo[b,f][1,4]thiazepin-11(10H)-one

Product 1

HCID 10269744HCID 10269744, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

8-Chloro-10H-dibenzo[b,f][1,4]thiazepin-11-one 2 (X=S and R1=Cl) (0.5 g, 1.91 mol), phosphorus oxychloride (5 ml, 53 mmol), toluene (25 ml) and N,N-dimethylaniline (1.0 ml) were heated at reflux for 3 hours. After evaporation of the volatiles, 25 ml of toluene and 5 ml (45 mmol) of 1-ethylpiperazine were added. Work-up and purification as described in Example 1 gave 150 mg (22%) of light yellow crystals, mp 100-101° C., 1H NMR (300 MHz, CDCl3), 1.11 (t, 3H, J=6.0 Hz, CH3), 2.55 (q, 2H, J=6.0 Hz, —CH2—), 2.55-2.65 (broad s, 4H, piperazinyl CH2), 3.55-3.65 (broad s, 4H, piperazinyl CH2), 6.83 (dd, 1H, J=1.5 and 6.0 Hz), 7.07 (d, 1H, J=1.5 Hz), 7.25-7.40 (mult., 4H), 7.50 (dd, 1H, J=7.5 Hz), MS (EI) m/z 357 (M+, 16.1%), 244(34.2), 209(30.1), 97(93.7), 84(100), HRMS calcd for C19H20N3SCl 357.1066, found 357.1067.

Workup

  1. temperatureat reflux for 3 hours
  2. additionwere added
  3. customWork-up and purification
  4. customgave 150 mg (22%) of light yellow crystals, mp 100-101° C., 1H NMR (300 MHz, CDCl3), 1.11 (t, 3H, J=6.0 Hz, CH3), 2.55 (q, 2H, J=6.0 Hz, —CH2—), 2.55-2.65 (broad s, 4H, piperazinyl CH2), 3.55-3.65 (broad s, 4H, piperazinyl CH2), 6.83 (dd, 1H, J=1.5 and 6.0 Hz), 7.07 (d, 1H, J=1.5 Hz), 7.25-7.40 (mult., 4H), 7.50 (dd, 1H, J=7.5 Hz), MS (EI) m/z 357 (M+, 16.1%), 244(34.2), 209(30.1), 97(93.7), 84(100), HRMS

Sources & evidence

ORD record
ord-58c93526ff7e4837a6bea40d6e42a3a3
Source dataset
uspto-grants-2005_05
Patent number
US06890919B2

Reaction notes

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